Fillies
Winning Colors (1988), owned by Eugene Klein, joined Mrs. Bertram R. Firestone's Genuine Risk (1980) and Mrs. H. P. Whitney's Regret (1915) as the only fillies to have won the Derby. She was third in the Preakness and sixth in the Belmont Stakes, joining Genuine Risk as the only other filly to have run in all three Triple Crown races.
Five of the 36 fillies to start in the Derby were post-time favorites. Two were Regret and Calumet Farm's Nellie Flag, fourth in the 1935 Derby. The H. P. Whitney entry of the filly Prudery and the colt Tryster was favored in the 1921 Derby. Prudery was third. The entry of Althea and Life's Magic was the 1984 favorite. Althea finished 19th and her stablemate, Life's Magic, was 8th.
| Year | Filly | Finish |
|---|---|---|
| 1875 | Ascension | 10th |
| 1876 | Gold Mine Lizzie Stone |
15th 6th |
| 1877 | Marie Michon Early Light |
7th 8th |
| 1879 | Ada Glenn Wissahickon |
7th 9th |
| 1883 | Pike's Pride | 6th |
| 1906 | Lady Navarre | 2nd |
| 1911 | Round the World | 6th |
| 1912 | Flamma | 3rd |
| 1913 | Gowell | 3rd |
| 1914 | Bronzewing Watermelon |
3rd 7th |
| 1915 | Regret | 1st |
| 1918 | Viva America | 3rd |
| 1919 | Regalo | 9th |
| 1921 | Prudery Careful |
3rd 5th |
| 1922 | Startle | 8th |
| 1929 | Ben Machree | 18th |
| 1930 | Alcibiades | 10th |
| 1932 | Oscillation | 13th |
| 1934 | Mata Hari Bazaar |
4th 9th |
| 1935 | Nellie Flag | 4th |
| 1936 | Gold Seeker | 9th |
| 1945 | Misweet | 12th |
| 1959 | Silver Spoon | 5th |
| 1980 | Genuine Risk | 1st |
| 1982 | Cupecoy's Joy | 10th |
| 1984 | Life's Magic Althea |
8th 19th |
| 1988 | Winning Colors | 1st |
| 1995 | Serena's Song | 16th |
| 1999 | Excellent Meeting Three Ring |
5th 19th |



















Ashley Walker
Jill Byrne
Dan Shapiro
John Asher
James Scully
Joe Kristufek